Azo dyestuffs



Fatent-ed Dec. 9, 193(9 U'NETED sra'rss PATENT QFFEECE .KARL J?HIESS, OFFBANKFORT-GN-THE-IfiAIN-HOCHST, GERMANY, ASSIGNQR TO GEN- ERAL ALN'ILINEWORKS, INC, OF NEW YGRK, N. Y., A CORPQEATIGN OF DELAWARE AZO DYESTUFFSNo Drawing. Application filed July 23, 1929, Serial No. 380,467, and. inGermany August 13, 1828.

The present invention relates to azo dye- I have found that yellowdisazo dyestuffs are obtained by coupling the diazo compound of a4.4:-diamino-triphenyl-methane derivative containing at least onehalogen atom in each of the three benzene nuclei with a-l-halogen-sulfo-aryl-3-alkyl-5-pyrazolone or a substitution productthereof. The new dyee stuffs thus obtained are distinguished by the pureshade they give and their good fastness properties, particularly bytheir fastness to fulling andlight.

I have furthermore found that yellow disazo dyestuffs of the same goodfastness properties are obtained by coupling al-halogensulfo-aryl-3-alkyl-5-pyrazolone or a substitution productthereof with the diazo compound of a 4.4-diamino-triphenyl-Inethanewhich has in each of the amino-containing benzene nuclei a halogen atomand a methyl group in ortho-position to the amino groups and which hasno halogen in the benzene nucleus free from an amino group.

the present invention correspond to the fol lowing general formula:

(\Na t W R for hydrogen or an alkyl group and wherein each of the twoaryl-residues con- The new dyestuffs obtainable according to Thestarting materials may be obtained by and coupling it with1-(2-chloro-5-sulfo)- phenyl-3-methyl-5-pyrazolone. The clyeings aredistinguished by their excellent fastness to fulling and light.

(2) A dyestuff dyeing a somewhat greener shade is obtained by couplingthe same tetrazotized dd diamino -trichloro triphenylmethane derivativewith 1-(2.5-dich]oro-dsulfo) -phenyl-3-1nethyl-5-pyraZolone.

(3) By tetraz-otizing a txy-diainino-triohloro-triphenyl-methanederivative of the following formula c i C H3 0 H3 NET-O (ENE: 01 oH c1tains halogen and a sulfo group, being green- 7 ish-yellow powders'whichdissolve in water 59 to a yellow solution.

and coupling it with l-(2,-chloro-5-sulfo)- phenyl3-inethyl-5-pyrazolone a water-soluble dyestuff is obtained dyeing woolvery vivid greenish-yellow tints of very good fastness properties. i V(4) By tetrazotizing .a- 4.{L-dia1nino-dichloro-triphenyl-methane,'derivative of the following constitution:

and coupling it with 1-(2-chloro-5'-sulfo)- phenyl-3-n1etliyl-5-pyrazolone a water-solu- 'ble dyestufi of very good fastness properties is obtained dyeing wool very vivid greenish-yellow tints. Ithns thefollowing 1. As new-products, the compounds of the following formula:

whereinw stends-for hydrogen or halogen, y

for halogen, z for hydrogen or a methyl group I and R for hydrogen or analkyl group and wherein each of the two aryl-residues contains halogenand a sulfo group, being greenish-yellow powders which dissolve in waterto alyellow solution.

2. As new products, compounds of th following formula; V r V e i 7 Nzlwherein a: stands for hydrogen or halogen, g for halogen, z for hydrogenore methyl group'end'n' for halogen, being greenishyellow powders whichdissolve in water to a yellow solution. J

' 3. iAs new vproducts, the compoundsof the following formula: r

i OH: I l

wherein m stands for hydrogen or halogen,

one y in each nucleus for halogen,- the other g in each nucleus forhydrogen, 2 for hydrogen or a methyl group and wherein each of the twoaryl residues contains halogen and a sulfo group, being greenish-yellowpowders which dissolve in water to a yellow solution.

7 4. As new product, the compounds of the following formula:

2:; we HJHQ Q Qmir A n I n A wherein m stands for hydrogen or halogen,

on, I

one 3 in each nucleus for halogen, the other 2 in each nucleus forhydrogen, a for hydrogen or a methyl group and n for halogen, beinggreenish-yellow powders which dissolve in water to a yellow solution.

5. As new products, the compounds of the following formula:

with 01 ll wherein m stands for hydrogen or halogen, beinggreenish-yellow powders which dissolve in water to a yellow solution.

6. As a new product, the compound of the following formula:

being a yellow powder which is soluble in water and which dyes wool veryvivid greenish-yellow tints of very good fastness to fulling and light.

In testimony whereof, I aflix my signa-ture.

KARL THIESS.

